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Photo: M.pvsk, CC BY-SA 4.0 via Wikimedia Commons
The main church of Valandovo was built in 1830. It features a prominent bell tower and contains icons dating from the 14th century. The church's current iconostasis was completed in 1989.
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Црква „Св. Ѓорѓи“
In the Middle Ages, an important and impressive church stood on the site today occupied by a 1934-built church that is small and quite average in appearance.
Исар Кале
This archaeological site dates from Late Antiquity, located to the northwest of the town on a hilltop above the Anska River. Most of what is left is remains of defense tower, but there fragments of ceramics and coins have also been found here.
Исар
The most significant archaeological site in this area dates from the 7th century BC to the 6th century AD. It sits on an elevation providing views of the Valandovo Valley and the Vardar River. The site consists of remains of an acropolis, a Roman city, fortifications, and a necropolis. Most of what can be seen today are building foundations and some pillars and archways, as well as building pieces with inscriptions. The site was first discovered during the First World War, but archaeological excavations remain underway today.
Црква „Св. Архангел Михаил“
Built in the mid-19th century, this church's frescoes were painted by the Donev brothers from Gari near Debar. The church also features a detached bell tower.
Спомен-костурница
This memorial chapel is found at the entrance to the village of Udovo. It was built to honor the fallen Serbian soldiers of World War I who died in this area. After Alexander I of Yugoslavia visited the area in 1931, he ordered the construction of the chapel. It was completed in 1936 and houses the remains of around 2,000 soldiers. The chapel is built of stone and capped by a dome. Udovo was a Turkish village a century ago, but is now home to an almost entirely Macedonian population of around 850 people.